Heterocyclic amino-oxazolines

ABSTRACT

of one through four carbon atoms; R&#39;&#39;&#39;&#39; is selected from the group consisting of hydrogen and methyl; and R&#39;&#39;&#39;&#39;&#39;&#39; is selected from the group consisting of hydrogen and methyl.

Unified Sinies Harem [72] Inventor George Levitt Wilmington, Del.

[21] Appl. No. 22,028

[22] Filed Mar. 23, 1970 [4S] Patented Dec. 14, 1971 [73] Assignee E. I.du Pont de Nemours and Company Wilmington, Del. Original applicationJune 12, 1967, Ser. No. 646,153, now Patent No. 3,511,851. Divided andthis application Mar. 23, 1970, Ser. No. 22,028

[54] HETEROCYCLIC AMINO-OXA ZOLINES 2 Claims, No Drawings 52 us. Cl260/288 7 [51] lnt.Cl... C0711 35/10, C07d 33/10 [50] Field of Search260/288 [56] References Cited UNITED STATES PATENTS 3,509,170 4/1970Levitt 260/288 X Primary Examiner-Donald G. Daus AttorneyD0n M. KerrABSTRACT: Amino-oxazolines useful as central nervous 31. .192dsusisrisksyi slh fsrm is wherein X is oxygen, sulfur or methylamino; Ris hydrogen or alkyl;

. R is hydrogen, alkyl, alkoxy, alkylthlo, dimethylamino, fluorine,chlorine or bromine;

HETEROCYCLIC AMINO-OXAZOLINES CROSS-REFERENCE TO RELATED APPLICATIONThis application is a divisional of my application Ser. No. 646,153,filed June I2, 1967 now U.S. Pat. No. 3,51 1.851.

BACKGROUND OF THE INVENTION Harvey, Ser. No. 313,756, filed Sept. 30,i963; granted as U.S. Pat. No. 3,432,600.

The present invention is directed to a new class of oxazolines havingcentral nervous system depressant activity.

SUMMARY OF THE INVENTION This invention relates to amino-oxazolines.More specifically this invention refers to compounds of the X is oxygen.sulfur or methylamino;

R is hydrogen or alkyl of one through four carbon atoms;

R is hydrogen, alkyl of one through four carbon atoms. alkoxy of onethrough four carbon atoms. alkylthio of one through four carbon atoms,dimethylamino, fluorine, chlorine, or bromine;

R" is hydrogen or alkyl ofone through four carbon atoms;

R' is hydrogen or alkyl ofone through four carbon atoms.

Preferred because of outstanding central nervous system depressantactivity are those compounds in formulas l.. 2., 3. and 4. in which X isoxygen or sulfur. R, R and R' are hydrogen and R is alkyl. alkoxy orhydrogen.

The manner and process of making and using this invention is describedin U.S. Pat. No. 3.5 l 1,85]. U.S. Class No. 260. Subclass No. 307.issued May l2. l970, the disclosure of which is herein incorporated byreference.

lclaim: l.

R, R 0-CII2 H N-C N- Hz X R% R! R R. OCH2 H NC Q NCH2 u X R l R OCH HN-C N--CH2 RI! X R!!! R R O-GH:

H l N-C N-CH2 X RI! RIH wherein Xis NCH R is selected from the groupconsisting of hydrogen and methyl;

R is selected from the group consisting of hydrogen; alkyl of onethrough four carbon atoms, and alkoxy of one through four carbon atoms;

R" is selected from the group consisting of hydrogen and methyl; and

R is selected from the group consisting of hydrogen and methyl.

2. A compound according to claim 1 which is 2-( 1.2.3.4- tetrahydrol-methyl-5-quinolinylamino)-2-oxazoline.

* t at k n:

2. A compound according to claim 1 which is2-(1,2,3,4-tetrahydro-1-methyl-5-quinolinylamino)-2-oxazoline.